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The Secret World of Hollywood Poker

Four-star hotels, food from Matsuhisa, masseuses -- the high-stakes game frequented by Tobey Maguire, A-Rod and A-list actors welcomed an unknown player in 2006 who now has brought them the kind of press no publicist wants.

They are among the highest of the high-stakes players in this moneyed town: A-list actors, Hollywood hangers-on and businessmen who can shell out $50,000 just for a seat at the table. With eight or nine gathered, they play no-limit hold 'em into the night at one another's multimillion-dollar homes in Beverly Hills, Bel Air, Brentwood or Malibu. Hundreds of thousands of dollars are won and lost -- sometimes in a single hand. They order in dinner from Matsuhisa or Madeo or tuck into filet mignon prepared by private chefs. They catch up on their busy lives, maybe discuss a business opportunity. All the while, the cards keep coming. When they tire, masseuses dole out massages. And at this level, the game is no longer simply about a group of buddies getting together for friendly bonding over cards. Indeed, this game -- and much of the world of high-stakes Hollywood poker -- is an intoxicating mix of competition, power and ego.

Nick Cassavetes and Gabe Kaplan are players, joined in the past by Leonardo DiCaprio, Matt Damon, Ben Affleck and on occasion, New York Yankees star Alex Rodriguez. But the star of these testosterone-fueled games, the celebrity who stands out in a group of millionaires and A-listers, is Tobey Maguire -- careful, conservative, effective.

It's a secretive gathering, one to which outsiders are typically denied entrance. Discretion is of paramount importance; trust is vital. But after several years of successful operation, that collective trust was breached. In March, players' names started appearing in court filings alleging that unbeknownst to them, they had been pocketing stolen money.

DiCaprio, Affleck, Damon and Rodriguez have never been mentioned in connection with the litigation, and most of the high-stakes players who were have settled. But two high-profile cases are pending. A court-appointed bankruptcy trustee is seeking the return of $311,200 from Maguire and $73,800 from Cassavetes -- plus interest. Both have retained counsel, and Maguire's attorney has vowed to fight.

The trouble began one day in summer 2006 when a hedge fund manager named Bradley Ruderman wandered off of exclusive Carbon Beach in Malibu and talked his way into the game. He appeared to be rich, affable, out for a good time. It would take years for the others to learn to their chagrin that he was not what he seemed.

In the meanwhile, they let him play and lose -- a lot. No-limit means that a player can wager any amount at any time. The most popular game in a town that has had a long love affair with poker in its many forms, no-limit hold 'em delivers the biggest highs and lows for those whose wealth and ennui leave them hungry for thrills. And it demands total concentration, making it a distraction from the day's anxieties. "You get in front of that green felt, and that's all you can think about," says one regular player.

All manner of Hollywood heavyweights are poker players, from former Warner Bros. chairman Bob Daly to Titanic and Avatar producer Jon Landau. Jeffrey Katzenberg has been known to turn up on a Sunday morning at the Commerce Casino outside Los Angeles for a game. But only a select few have the means and desire to play at the highest levels of wagering. "This Texas hold 'em stuff can get pretty serious," says former Warner Bros. president Alan Horn, who hosts a far less intense poker game -- dealer's choice -- at his house. "It's another animal. I mean, we're all animals, but we're playing the gazelle version and the guys across the watering hole are playing the lion-and-tiger version."

By most accounts, Ruderman was prey, a "fish," in poker parlance, who obliged his fellow players by losing. "A fish is somebody that just regularly donates," says one of Hollywood's veteran poker players. "Believe me -- these guys want patsies. … It's not easy finding players at this level."

Ruderman may have been a bad player, but he must have been a pretty good actor because the wealthy hedge-fund manager turned out to be a con man, a mini-Madoff who was charged with running a $44 million Ponzi scheme that targeted his friends and family and bilked investors out of more than $25 million. Since his 2009 conviction, he has been serving a 10-year sentence in a Texas prison. But once his company, Ruderman Capital Partners, was forced into bankruptcy, his Hollywood friends -- some of whom had pocketed easy winnings from him -- suddenly found themselves on the receiving end of litigation. A court-appointed trustee has moved to claw back the ill-gotten gains that Ruderman had lost at the poker table. The whole ugly mess has brought with it unwelcome publicity and raised the specter of something darker than a simple night out with the boys.

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Poker in Hollywood defies simple description: there are many gatherings at many levels, and while all seem to be intensely competitive, each game acquires its own personality. "Poker comes in all sizes," says a well-known film producer who plays every week with a buy-in of a few thousand dollars. "There is no rule. Don't look for a definition of games of poker."

Some Hollywood players favor home games, while others flock to Los Angeles-area casinos, of which there are several. When Landau is in town, for example, he sometimes visits the Commerce Casino, now the largest card room in the world. "Other people go golfing, I go to Commerce. I'll go in the morning on a Sunday, watch the first football game, play poker and then meet my family for an afternoon out," says Landau, who collects a chip from each of the casinos he visits around the world and keeps the mementos from Russia, Spain and England in a picture frame he displays at home.

But the most popular game is hold 'em, which became more alluring in recent years thanks to improvements in the way that tournaments were broadcast on television, allowing viewers to peek at the face-down cards. It probably didn't hurt that during the same era, the game was glamorized in such films as the Damon-starring Rounders (1998) and Ocean's Eleven (2001) and Casino Royale (2006). "There was a sea change at the turn of the century," says John De Simio, executive vp of the Broadcast Film Critics Association and a regular player in Horn's game. "That is when Texas hold 'em became the king."

"Poker is the new millennium's golf course," says actor Joshua Malina, who co-created Bravo's Celebrity Poker Showdown series in 2003. "Over poker, a lot of friendships and business relationships are made." His own experience illustrates the point: He started playing poker years ago in New York in a game hosted by Aaron Sorkin. Eventually a relationship that was partially cemented over poker games led to roles in Sorkin's Sports Night and The West Wing. After moving to Los Angeles in 1992, Malina became a regular in another gathering with Hank Azaria, then with a relatively modest $500 buy-in. (Over time, Malina dropped out of those games as the stakes grew richer.)

The film producer who plays each week concurs that poker adds a little grease to the industry machine -- within limits. "If you put seven people who are all in show business in a room, they talk about business," he says. "You think they don't say, 'What do you think about The Help grosses?' But is anyone going to buy CBS in a game? It's not the Allen & Company conference."

Many games, like Horn's gatherings on Tuesday nights once or twice a month, are relatively low-key. "The stakes are high enough to be a little interesting," Horn says. But he says no one takes the game too seriously. "It's meant to be a night where we sit around, have some food and don't think about whatever else is going on in life," he says. The crowd there --mostly old friends from his days running Castle Rock -- plays less intense games like seven-card stud or Omaha, with a buy-in of $1,000. Landau, who hosts a home game with a $300 buy-in, says the stakes are low enough in his game that "anybody can come and sit down. You want to win, but if someone loses one night at our house, it doesn't change their life."

Daly says much the same of his regular poker game with friends -- including Horn, Katzenberg and Joe Roth -- in which the buy-in is $1,000. "I only hear about hold 'em," he says. "Some of these games are way beyond anything I could dream of. … I wouldn't even dream about playing in them because I've worked too hard for my money to lose it in a poker game."

The serious hold 'em players also insist the games are harmless diversions, albeit with much higher stakes. Yet the players tend to be strikingly defensive and unwilling to talk about a pastime that in some cases seems to occupy a considerable part of their time. No current player was willing to speak for the record, but THR found one insider who agreed to discuss the game on condition that his name not be used. According to that source, some of the celebrity players started out frequenting local places like the Commerce Casino, but they quickly found gambling in that setting to be cumbersome and unpleasant. "They would have to deal with the people and the paparazzi while trying to have a card game," this insider says. "They can't really go to public card rooms. They're wealthy and they want to have friends over and play poker. It's no different from club members playing high-stakes gin at any of the country clubs on the Westside."

The players, several already friends, retreated to the privacy of a home game and to luxury suites in the Peninsula or Four Seasons hotels. Over time, a larger group of like-minded individuals began playing regularly, though the roster changed over the years. According to the insider, the burgeoning game started with a $5,000 buy-in that eventually increased to $50,000. While such an escalation may sound dizzying to ordinary people, the film producer who plays in smaller games points out that everything is relative. "The people who are buying in for $50,000 -- it probably means as little to them as $5,000 means to me," he says.

For serious players, it seems, the size of the wagers always increases. Malina, who couldn't really afford to go much beyond the $500 buy-in of the early Azaria games, admits that he finds those big numbers intoxicating. "It's like drugs, I imagine," he says. "It's baked into the alchemy of poker that you keep wanting to raise the stakes. … People tend to play just at that level where it hurts or feels very good."

In Malina's view, actors find that no-limit hold 'em has particular allure. "There is a huge element of acting," he says. "It's all about controlling your emotions … not revealing anything, giving false signals. There's a swaggering aspect: I'm going to psychologically beat you down and take your money. Actors, ego-driven animals that they are, they are drawn to that kind of warfare."

It is not solely actors who have played in the big hold 'em game -- there had to be others. Not many people can afford the buy-in, but among those who easily have made the cut are Alec Gores, the billionaire investor; Rick Salomon, famous for the sex tape he made with Paris Hilton; Joe Francis, creator of Girls Gone Wild; and on occasion, Yankees third baseman Rodriguez. Most declined to comment or did not return phone calls, though some responded to THR through their attorneys, as was the case for most of the players with Hollywood credits.

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According to the insider, the big games were simply gatherings of friends looking to bond and relax. But by the summer of 2006, these games were hardly spontaneous get-togethers but more structured affairs, managed by an attractive, then-28-year-old brunette named Molly Bloom.

Bloom, whose brother Jeremy is a former Olympic skier and now an ESPN college football analyst, allegedly had myriad responsibilities. According to court filings, she was paid to set up hotel suites for games, relay information to the players and hire dealers as well as arrange for food, drinks, massages and bodyguards. Bloom also kept track of winnings and losses and arranged for payment to be made among players.

Ruderman came into this very exclusive game in an unlikely fashion: He had been renting an oceanfront Carbon Beach residence next door to the house of a player. One day, he walked over while a game was under way and introduced himself. "He was a quirky, quiet guy and easy to play with, and that's how he got involved with it," the insider says. Perhaps Ruderman's charm also lay in the fact that he lost, a lot.

"I don't think any serious poker player has a problem taking money from somebody who is bad at it," Malina says. "I wouldn't want to take money from someone who can't afford it. But a rich guy -- which he appeared to be -- yeah. You have to have that killer instinct as a poker player. A poker player wants to take whoever's money is easiest to take. The metric I apply is how much money I won. More is better. Most honest poker players will tell you that."

And it did appear that Ruderman could pay. The eldest child of a financial adviser, Ruderman had grown up in Los Angeles. After graduating from UCLA with a degree in political science in 1986, he had moved to New York, where he worked as an investment banker at several Wall Street firms including Lehman Bros. Eventually he returned to Los Angeles and, starting in 2002, convinced a group of investors, including family members, to entrust him with their money.

He boasted that his Ruderman Capital Partners hedge funds generated returns as high as 60 percent with stakes in such companies as Apple and Walmart. And he played the role of the successful investor. In a period of a few years, according to court papers, he laid out at least $8.7 million on such personal expenses as two Porsches and that pricey summer rental in Malibu.

The fact that Ruderman apparently slipped into the game without an introduction might have eliminated a layer of protection. Usually, says the film producer who plays regularly in smaller games, the person who introduces a new player is vouching implicitly that the newcomer can handle the stakes. But ultimately, this producer says, anyone who enters a game is vouching for himself. "If a guy comes into your game, he is saying, 'I can pay.' It's nobody's responsibility to make sure a guy can pay -- unless you bring them to the game," he says.

When the economy dipped in 2008, things began to fall apart for Ruderman. Not only was the Ponzi scheme proving unsustainable, but he had blown a fortune at the poker table. According to court filings, he had racked up a staggering $5.2 million in poker losses -- as little as roughly $20,000 to one player and nearly $1 million to another.

Ruderman kept playing until March 2009, a month before Ruderman Capital was forced into involuntary bankruptcy. On May 15 of that year, Ruderman, then 46, surrendered to FBI agents. He was charged with running the Ponzi scheme that bilked investors out of more than $25 million. Among those left holding the bag in the bankruptcy is Gores, who is owed $4 million because he had invested his own money with Ruderman. (With a net worth of $1.9 billion, Gores is No. 227 on Forbes' list of the richest Americans. His brother, Sam Gores, heads the Paradigm talent agency, and another, Tom Gores, owns the NBA's Detroit Pistons.)

According to Ruderman's own account as told in court papers, he had continued to play poker as his losses mounted, convincing himself that he could win back the money even while recognizing that was virtually impossible. That kind of thinking is typical for an addict, according to a former actor who developed a gambling habit after becoming a regular at Texas hold 'em games. "It grabs you from every angle," he says. "If you're winning, you feel like the king of the world. If you're losing, you think, 'How am I going to get out of this?' You gamble more."

Following his arrest, Ruderman declared that he was, in fact, an addict. While his legal fate was being decided, he moved into the Beit T'Shuvah Residential Treatment Program in Los Angeles. (The program, which involves faith-based treatment, was co-founded by Ruderman's father for philanthropic reasons years before he imagined that his son would end up living there.) In a medical evaluation submitted to the court, Dr. Timothy Fong of the UCLA Gambling Studies Program wrote that prolonged incarceration would prevent Ruderman from getting the care he needed and increase the likelihood of relapse. The judge was not convinced. In January 2010, Ruderman was sentenced to 121 months in a minimum-security federal prison in Big Spring, Texas.

Contacted there, Ruderman was initially eager to tell his story, to discuss the nature of gambling addiction and the culture of poker in Hollywood. He agreed to a meeting at prison as long as family did not object. But Ruderman's family did object, and the offer was withdrawn.

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As it turned out, the fish had bluffed the sharks. He was not one of them. And thanks to Ruderman, details of the secretive poker game have come to light in public documents filed by the court-appointed trustee overseeing the bankruptcy of Ruderman's failed firm. Attempting to retrieve as much money as possible for those who were fleeced, trustee Howard Ehrenberg has gone to court, demanding that winners in that high-stakes game give back the money they had won from Ruderman.

Ehrenberg, a bankruptcy expert with law firm SulmeyerKupetz, argues that the poker players were not entitled to their winnings because Ruderman paid his debts with "improperly diverted investors' funds" from the Ponzi scheme. The trustee also argues that the games were illegal because the players paid Bloom to arrange them. That transformed the gatherings from legal home games to "controlled" games, which require a license from the state of California, he argues. Though no criminal charges are expected to be brought, legal experts say the characterization of the game as an illegal operation makes it harder for defendants to fend off the trustee's efforts to recoup their winnings.

Ehrenberg has sued 24 players and so far has reached settlements with 14 defendants, recovering $1.63 million; in total, he has recovered $5.05 million for the estate. In August, Gores, who won $445,400 from Ruderman, agreed to return $150,522; Kaplan, who won $62,000, agreed to return $27,900. "It is our view that the games were not illegal," says Patricia Glaser, attorney for Gores and Kaplan. But both settled for less than 50 percent of what they won from Ruderman. It's possible that legal fees associated with fighting the cases would have been more costly for the defendants than settling.

Salomon, winner of $23,000, returned $10,000. Attorney Joseph Costa, who represents Salomon, says his client's decision to settle was solely driven by economic considerations. "We don't believe there was anything inappropriate regarding any of the activities that went on, and to the extent they are seeking the return of monies, there are defenses to what they are alleging. There was no admission of liability or any wrongdoing by Salomon at all," he says.

Cassavetes' attorney, Ronald Richards, is expected to answer the trustee's lawsuit in the next month. Richards is representing four poker players involved in the bankruptcy proceeding.

Maguire's attorneys have noted in filings that he lost $168,500 to Ruderman in the high-stakes game and say he should therefore pay a sum reduced by that amount, if he is required to pay at all. The lawyers also have argued that the games were not illegal, and if money paid by Ruderman to him was improperly taken from Ruderman Capital, the actor didn't know it.

By several accounts, Maguire is an especially careful and skilled player, perhaps the best on the celebrity circuit. He has won a total of $51,669 in three World Series of Poker showings and placed 54th in the 2005 event. According to Francis, Maguire keeps a card-shuffling machine in the trunk of his car.

A court-ordered mediation is scheduled for November in Maguire's case, with a trial set for June 18. "The dispute with the trustee is a business dispute that is to be adjudicated in the court, and Tobey Maguire expects to be vindicated in this proceeding," a spokesperson for the actor says.

Ehrenberg is counting on the court to agree with him. The trustee says he'd hoped to settle the entire matter quietly and never intended to embarrass the celebrity players. "Am I surprised that somebody wants to defend themselves? No," he says. "Do I think they're going to win? No."

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The insider interviewed by THR is upset by the suggestion in court papers and press reports that the games in question were illegal and even unsavory. "They're trying to find something sinister about it," he says. "All of this stuff has been going on for a long, long time, whether it's this group or another group. This is just a bunch of guys who like to hang out together, spend time together and happen to enjoy playing poker."

He also denies that Bloom was paid to arrange and perform other duties in connection with the games. "This game never had that," he says. "We'll never have that." He says that Bloom was only paid in large tips.

But legal documents show that from May 2007 to November 2008, Ruderman transferred a total of $473,200 to Bloom. In court filings, bankruptcy trustee Ehrenberg has argued that the money was used at least in part to pay Bloom for her services. He is suing Bloom to recover the money. In a June court filing, Bloom's attorneys denied that she ran a controlled poker game but acknowledged that she received money from Ruderman "in good faith in exchange for her services." A trial has been set for May 29. Bloom was initially represented in the bankruptcy litigation by Richards, the same attorney who represents Cassavetes and other players. Richards tells THR that Bloom is no longer a client. Her current lawyer, Sara Chenetz of Blank Rome Llp., declined to comment.

Ehrenberg has taken Bloom's deposition, which has not been made public. But in it, according to a report in Star magazine, she reportedly acknowledged regularly hiring masseuses to tend to the tired players.

Bloom remains an intriguing and shadowy character in the poker drama. She is no stranger to scrapes with the law. She grew up in Loveland, Colo., a conservative midsize city with a sizable evangelical population. Raised by parents Larry, a clinical psychologist, and Charlene, a ski and fly-fishing instructor, Bloom and her two younger brothers were avid skiers. In 1997, she was sentenced to 30 days in jail after pleading guilty to speeding. And in 1999 and 2001, she would plead guilty to speeding and driving with expired license plates.

After moving to Hollywood in 2003, Bloom worked as an assistant to Darin Feinstein, a part-owner of the Viper Room who played in the big game, according to sources. A few years later, in November 2007, she started Molly Bloom Inc., an event-planning business with an address in a West Hollywood residential building. (It is no longer an active corporation.)

It is unclear when Bloom began making arrangements for the high-stakes poker game, but obviously she won the trust of the players and reportedly said in her deposition that she had a "social relationship with most of [them]." Court filings show that Ruderman made his first payment to her -- $10,500 -- in May 2007.

Girls Gone Wild creator Francis, who played in the big games from 2003 to 2007, says Bloom has fallen out of favor with the players. "Look, I've talked to all of the boys who played in the game," he says. "I know all those guys hate her now." Francis says he played at games at which Bloom was in attendance and her duties ranged from handling collections to mixing cocktails. Francis, who is not named in the bankruptcy filings, also insists that the games were legal and says Bloom only received tips from players, including regular $5,000 handouts from him.

Certainly, things seem to have gone sour for Bloom since those days. Sometime in 2009 -- apparently before Ruderman turned himself in -- Bloom relocated to New York. It is unclear what precipitated her move. The New York Post reported that Bloom started a poker game in Manhattan, arranging for sessions at the Astor Place and Plaza hotels and recruiting women from nightclubs to attend. But a lack of New York connections made it tough for Bloom, and she moved her game -- which featured a buy-in of roughly $10,000 -- to Long Island.

In July 2010, Bloom was served with a $116,133 lien for not paying taxes on her income in New York. The Star also reported in June that after she had moved to Manhattan in 2009, Bloom had received a beating at the hands of "two Eastern European thugs." Her attorney at the time confirmed the attack and discounted suggestions that the incident was related to poker. Bloom is said to have moved again in June, this time to Malibu.

According to the insider, scandal and litigation have taken a toll on the game. While the players used to meet every week, they're lucky now if they get together twice a month. Yes, the recession is partly to blame; it forced some players to be more judicious with their money. But more than anything, the fallout from Ruderman has caused at least some of the players to take a step back.

The legal issues have proved taxing for some. The insider says the Ruderman matter has caused the group to circle the wagons and handle the game more cautiously. Though he remains a staunch defender of it, he finds he is playing less often. "These kinds of things take the wind out of your sails," he says. "Even when you win, you lose."